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CS-W001157 4
Total: USD 88.00

4-Hydroxy-3-methoxy-2-nitrobenzaldehyde

  • CAS No. 2450-26-2

  • Cat. No. CS-W022193
  • Purity≥98%
  • MDL No.MFCD00017020

*For research and further manufacturing use only, not for direct human use.

4-Hydroxy-3-methoxy-2-nitrobenzaldehyde|CS-W022193

Structure of 2450-26-2

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General Information

  • CAS No. 2450-26-2
  • Cat. No. CS-W022193
  • Purity ≥98%
  • MDL No. MFCD00017020
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇NO₅
  • Molecular Weight 197.14
  • Synonym(s) NSC 95689
  • SMILES O=CC1=CC=C(O)C(OC)=C1[N+]([O-])=O

Description

4-Hydroxy-3-methoxy-2-nitrobenzaldehyde features a nitro group at the ortho position relative to the aldehyde, enhancing electrophilicity for nucleophilic addition. The phenolic hydroxyl and methoxy substituents provide steric and electronic modulation, enabling selective functionalization in complex synthesis. This bench-stable reagent integrates readily into multi-step sequences requiring controlled reactivity.

Application

4-Hydroxy-3-methoxy-2-nitrobenzaldehyde serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling efficient access to substituted benzimidazoles, quinones, and bioactive heterocycles. Its ortho-nitro and aldehyde functionalities facilitate sequential transformations under mild conditions, while the phenolic hydroxyl and methoxy groups offer sites for derivatization. The compound exhibits good bench stability and is amenable to standard purification techniques, making it well-suited for scalable synthesis workflows.

Synthesis

  • Route1
    • 4-formyl-2-methoxy-3-nitrophenyl acetate|CS-0000135
      2698-69-3
    • ~96%
    • In-stock
      4-Hydroxy-3-methoxy-2-nitrobenzaldehyde|CS-W022193
      2450-26-2

    References

    • Bayer Healthcare AG Patent: WO2004/29055 A1, 2004 ; Location in patent: Page 51 ; WO 2004/029055 A1
  • Route2

    References

    • Nimgirawath, Surachai; Udomputtimekakul, Phansuang; Taechowisan, Thongchai; Wanbanjob, Asawin; Shen, Yuemao Chemical and Pharmaceutical Bulletin, 2009 , vol. 57, # 4 p. 368 - 376
  • Route3

    References

    • Journal of Organic Chemistry, , vol. 60, # 17 p. 5494 - 5503

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   89.67
  • LogP   1.1215
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   3

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